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Phosphorus oxychloride → Methyl-2-(3-fluoro-2-methyl-benzyl)-3-formyl-1-phenyl-indolizine-7-carboxylate

HRID 1963054
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HRID 1963054 반응식
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][N:13]2[C:17]([CH:18]=1)=[C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[CH3:33])=[CH:14]2)=[O:9].[C:34]([O-])(=[O:36])C.[Na+]>CN(C=O)C.O>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][N:13]2[C:17]([CH:18]=1)=[C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[CH3:33])=[C:14]2[CH:34]=[O:36])=[O:9]
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참가 물질

6

반응물 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 67771873Methyl-2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-7-carboxylate

생성물 1

HCID 88414465Methyl-2-(3-fluoro-2-methyl-benzyl)-3-formyl-1-phenyl-indolizine-7-carboxylate수율 58.3%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매
3회

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온도
60 °C

실험 절차

To phosphorus oxychloride (0.35 ml, 3.82 mmol) cooled at 0° C. under argon, was added dropwise anhydrous DMF (0.34 ml, 4.46 mmol) and the mixture was stirred for 5 min forming a precipitate. 1.5 ml of DMF were added and stirring was continued at 0° C. for 15 min. To this mixture was added dropwise a solution of the compound of step 2 (0.476 g, 1.27 mmol) in 5 ml of DMF, and the mixture was heated at 60° C. for 1.5 h and then stirred at room temperature overnight. A solution of sodium acetate (0.837 g) in 6.5 ml water was added, the mixture was heated at 50° C. for 1 h, and evaporated to dryness under reduced pressure. The residue was dissolved in EA, the solution was washed with a saturated solution of sodium hydrogencarbonate, water and brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0, then 90:10) to give 0.297 g of the title compound.

후처리

  1. customforming a precipitate
  2. stirringstirring
  3. waitwas continued at 0° C. for 15 min
  4. stirringstirred at room temperature overnight
  5. temperaturethe mixture was heated at 50° C. for 1 h
  6. customevaporated to dryness under reduced pressure
  7. dissolutionThe residue was dissolved in EA
  8. washthe solution was washed with a saturated solution of sodium hydrogencarbonate, water and brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated to dryness under reduced pressure
  12. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0

출처 및 근거

ORD 기록
ord-b45deb4c148a46cf96b46cb7e2c29b08
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415336B2

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